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BEC HCl

Alias: S-(2-boronoethyl)-L-cysteine BEC HCl
Cat No.:V5730 Purity: ≥98%
BEC HCl is a slow-binding competitive Arginase II inhibitor (antagonist) with Kis of 0.31 μM and 30 nM at pH 7.5 and pH 9.5, respectively.
BEC HCl
BEC HCl Chemical Structure CAS No.: 222638-67-7
Product category: Arginase
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of BEC HCl:

  • BEC
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Top Publications Citing lnvivochem Products
Product Description
BEC HCl is a slow-binding competitive Arginase II inhibitor (antagonist) with Kis of 0.31 μM and 30 nM at pH 7.5 and pH 9.5, respectively.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Using hemihedral completely twinned crystals, the X-ray crystal structure of the arginase-BEC complex has been established at a resolution of 2.3 Å. The complex's structure demonstrates that a metal-bridging hydroxide ion nucleophilically attacks the boronic acid moiety, resulting in the formation of a tetrahedral borate anion that bridges the dinuclear manganese cluster. This mimics the tetrahedral intermediate and its flanking ions in the transition state of the arginine hydrolysis reaction [2].
ln Vivo
Increased S-nitrosylated and nitrated proteins are seen in the lungs of inflamed mice after the arginase inhibitor BEC is administered. This decreases arginase activity and alters NO homeostasis. BECs promote mucus metaplasia, NF-κB DNA binding, mRNA production of the NF-κB-driven chemokine genes CCL20 and KC, and perivascular and peribronchiolar lung inflammation. They also cause further increases in airway hyperresponsiveness [3].
Animal Protocol
Animal/Disease Models: C57BL/6J wild-type mice, arginase 2-deficient mice (Arg2-/-), arginase 1 and arginase 2-deficient mice (Arg1-/-Arg2-/ -), NOX2-deficient mice (NOX2-/-
Doses: 20 mg/kg.
Route of Administration: 1 hour before LPS injection, intravenous (iv) (iv)injection of 0.9% saline.
Experimental Results: BEC Dramatically diminished glial cells (72% reduction) and VEGF expression in macrophages/microglia (87% reduction).
References

[1]. Classical and slow-binding inhibitors of human type II arginase. Biochemistry. 2001 Aug 7;40(31):9356-62.

[2]. Probing erectile function: S-(2-boronoethyl)-L-cysteine binds to arginase as a transition state analogue and enhances smooth muscle relaxation in human penile corpus cavernosum. Biochemistry. 2001 Mar 6;40(9):2678-88.

[3]. Inhibition of arginase activity enhances inflammation in mice with allergic airway disease, in association with increases in protein S-nitrosylation and tyrosine nitration. J Immunol. 2008 Sep 15;181(6):4255-64.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C5H13BCLNO4S
Molecular Weight
229.482
Exact Mass
229.035
CAS #
222638-67-7
Related CAS #
222638-67-7 (HCl);63107-40-4;
PubChem CID
91826515
Appearance
White to yellow solid powder
LogP
0.106
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
6
Heavy Atom Count
13
Complexity
145
Defined Atom Stereocenter Count
1
SMILES
B(CCSC[C@@H](C(=O)O)N)(O)O.Cl
InChi Key
GHPYJLCQYMAXGG-WCCKRBBISA-N
InChi Code
InChI=1S/C5H12BNO4S.ClH/c7-4(5(8)9)3-12-2-1-6(10)11;/h4,10-11H,1-3,7H2,(H,8,9);1H/t4-;/m0./s1
Chemical Name
(2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid;hydrochloride
Synonyms
S-(2-boronoethyl)-L-cysteine BEC HCl
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ~50 mg/mL (~217.87 mM)
DMSO : ~50 mg/mL (~217.87 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.89 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (10.89 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (10.89 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 140 mg/mL (610.05 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.3577 mL 21.7884 mL 43.5768 mL
5 mM 0.8715 mL 4.3577 mL 8.7154 mL
10 mM 0.4358 mL 2.1788 mL 4.3577 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT03389022 UNKNOWN STATUS Drug: Ketamine
Drug: Saline
Drug: Ketamine
Bariatric Surgery Candidate
Pain, Postoperative
Lithuanian University of Health Sciences 2015-07-22 Phase 4
NCT04483024 COMPLETED Dietary Supplement: Collagen
hydrolysate and chicken extract
Knee Osteoarthritis
Muscle Loss
Shan May Yong 2018-12-01 Phase 1
Biological Data
  • Effects of the arginase inhibitor, BEC, on OVA-induced inflammation and arginase activity. A, Arginase I protein expression was analyzed in sections from paraffin-embedded lungs by polyclonal Ab and secondary conjugated with Alexa Fluor-568 (red). Nuclei were counterstained with Sytox Green (green). Images are presented at a magnification of ×200. B, Assessment of arginase activity in cells collected from BAL from control mice (Alum/OVA) or mice with allergic inflammation (OVA/OVA) 24 or 48 h postadministration of BEC. *, p < 0.05 using ANOVA, compared with the OVA/OVA group. C, Evaluation of arginase inhibition in primary mouse tracheal epithelial cells after incubation with 1 or 5 mM BEC in absence of l-arginine or in the presence of 100, 250, or 500 mM l-arginine. *, p < 0.05 using ANOVA, compared with sham groups. D, Assessment of differential cells counts in BAL fluid in control mice (Alum/OVA) or mice with allergic inflammation (OVA/OVA) in response to administration of PBS or BEC. E, Analysis of OVA-specific IgE from plasma of mice nonsensitized and sensitized and challenged with OVA treated with PBS or BEC via ELISA. *, p < 0.05 using Student's t test, compared with the OVA/OVA group. Values are corrected mean OD ± SEM) from n = 4–5 mice per group.[3]. Ckless K, et al. Inhibition of arginase activity enhances inflammation in mice with allergic airway disease, in association with increases in protein S-nitrosylation and tyrosine nitration. J Immunol. 2008 Sep 15;181(6):4255-64.
  • The arginase inhibitor BEC enhances peribronchiolar and perivascular inflammation in mice sensitized and challenged with OVA. Lung histopathology was evaluated by staining paraffin embedded sections from lung airways (A) and vasculature (C). Histological scores of peribronchiolar (B) and perivascular inflammation (D), at a magnification of X200. *, p < 0.05 ising Student's t test, compared with the OVA/OVA group. E, Assessment of airway hyperresponsiveness using forced oscillation invasive mechanics (40, 41). Shown are the respiratory mechanics for a measure of airflow heterogeneity or tissue resistance (parameter G) and a measure of airway closure/elastance (parameter H) in response to a methacholine dose of 50 mg/ml. The parameter Newtonian Resistance (R) was not affected by BEC (data not shown). *, p < 0.05 by ANOVA, denotes differences in peak responses, compared with the OVA/OVA groups. #, p < 0.05 by ANOVA, denotes differences in the timing of the peak response, compared with the OVA/OVA groups. The left segment of the x-axis represents two measurements, 10 s apart before methacholine dose of 50 mg/ml. Data are representative of experiments performed twice on n = 4–8 mice per group.[3]. Ckless K, et al. Inhibition of arginase activity enhances inflammation in mice with allergic airway disease, in association with increases in protein S-nitrosylation and tyrosine nitration. J Immunol. 2008 Sep 15;181(6):4255-64.
  • Evaluation of mucus metaplasia, IL-13 and CLCA3 gene expression in lung tissue from mice sensitized and challenged with OVA and submitted to PBS or BEC treatment. A, Representative sections from paraffin-embedded lungs, stained using periodic acid Schiff reagent to visualize mucus producing cells in the airways, at a magnification of ×200. B, Airways were scored for the extent of periodic acid Schiff reactivity, by two independent, blinded observers, and the averaged scores were recorded. RNA was collected from lungs, reverse-transcribed, and analyzed for IL-13 (C) and CLCA3 (D). Total lung cDNA was analyzed by quantitative PCR, and the data were normalized to the housekeeping gene, β-actin. Data are expressed as mean relative expression ± SEM from n = 4 to 8 mice per group. *, p < 0.05 by the Student t test, compared with the OVA/OVA group.[3]. Ckless K, et al. Inhibition of arginase activity enhances inflammation in mice with allergic airway disease, in association with increases in protein S-nitrosylation and tyrosine nitration. J Immunol. 2008 Sep 15;181(6):4255-64.
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